FR2822467B1 - BENZOXATHIEPIN DERIVATIVES AND THEIR USE AS MEDICAMENTS - Google Patents

BENZOXATHIEPIN DERIVATIVES AND THEIR USE AS MEDICAMENTS

Info

Publication number
FR2822467B1
FR2822467B1 FR0103877A FR0103877A FR2822467B1 FR 2822467 B1 FR2822467 B1 FR 2822467B1 FR 0103877 A FR0103877 A FR 0103877A FR 0103877 A FR0103877 A FR 0103877A FR 2822467 B1 FR2822467 B1 FR 2822467B1
Authority
FR
France
Prior art keywords
alkyl
preparing
derivatives
arylthiopropylamino
aryloxathiepine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
FR0103877A
Other languages
French (fr)
Other versions
FR2822467A1 (en
Inventor
Bernard Vacher
Cuisiat Florence Castan
Gareth Wyn John
Bruno Legrand
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Pierre Fabre Medicament SA
Original Assignee
Pierre Fabre Medicament SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to FR0103877A priority Critical patent/FR2822467B1/en
Application filed by Pierre Fabre Medicament SA filed Critical Pierre Fabre Medicament SA
Priority to EP02759802A priority patent/EP1370547B1/en
Priority to AU2002308105A priority patent/AU2002308105B2/en
Priority to PT02759802T priority patent/PT1370547E/en
Priority to CA2441534A priority patent/CA2441534C/en
Priority to DK02759802T priority patent/DK1370547T3/en
Priority to ES02759802T priority patent/ES2227481T3/en
Priority to CNB028091450A priority patent/CN1264836C/en
Priority to JP2002579452A priority patent/JP4508531B2/en
Priority to PCT/FR2002/000969 priority patent/WO2002081464A1/en
Priority to BRPI0208324A priority patent/BRPI0208324B1/en
Priority to DE60201264T priority patent/DE60201264T2/en
Priority to US10/472,728 priority patent/US7109234B2/en
Priority to AT02759802T priority patent/ATE276240T1/en
Priority to MXPA03008570A priority patent/MXPA03008570A/en
Publication of FR2822467A1 publication Critical patent/FR2822467A1/en
Priority to ZA200307362A priority patent/ZA200307362B/en
Application granted granted Critical
Publication of FR2822467B1 publication Critical patent/FR2822467B1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/06—Antiarrhythmics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Biomedical Technology (AREA)
  • Cardiology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

3-(arylthiopropylamino)-1,5-aryloxathiepine derivatives (I) are new. 3-(arylthiopropylamino)-1,5-aryloxathiepine derivatives of formula (I) and their (hydrated) addition salts with (in)organic acids, tautomers, enantiomers and stereoisomers are new. R1 and R2 = H, fluoro, chloro, hydroxy, 1-3C alkyl, cyclopropyl, cyclopropoxy; or R1 +R2 = 5-membered non-aromatic ring, optionally including an oxygen atom; R3 = 1-3C alkyl, hydroxy or MeO; R4 = H or Me; and R5 and R6 = hydrogen, 1-3C alkyl, alkoxy or alkylthio, or alkylamino. Provided that when R4 is Me, the R5 is not alkyl, or OR4 and R5 complete a 5- or 6-membered ring containing at least one oxygen. Independent claims are also included for: (1) Methods for preparing (I); (2) Intermediate amines of formula (VI); (3) Method for preparing (I); (4) Aldehydes of formulae (II) and (V); and (5) Methods for preparing (II) and (V). R3 = 1-3C alkyl or MeO; and R4 = Me in (II) or methoxymethyl in (V).
FR0103877A 2001-03-22 2001-03-22 BENZOXATHIEPIN DERIVATIVES AND THEIR USE AS MEDICAMENTS Expired - Fee Related FR2822467B1 (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
FR0103877A FR2822467B1 (en) 2001-03-22 2001-03-22 BENZOXATHIEPIN DERIVATIVES AND THEIR USE AS MEDICAMENTS
BRPI0208324A BRPI0208324B1 (en) 2001-03-22 2002-03-20 compounds, compound preparation process, and pharmaceutical compositions
PT02759802T PT1370547E (en) 2001-03-22 2002-03-20 BENZOAXATIPINES DERIVATIVES AND THEIR USE AS MEDICINES
CA2441534A CA2441534C (en) 2001-03-22 2002-03-20 Benzoaxathiepin derivatives and their use as medicines
DK02759802T DK1370547T3 (en) 2001-03-22 2002-03-20 Benzoxathiepine derivatives and their use as pharmaceuticals
ES02759802T ES2227481T3 (en) 2001-03-22 2002-03-20 BENZOAXATIEPINAS DERIVATIVES AND ITS USE AS MEDICINES.
CNB028091450A CN1264836C (en) 2001-03-22 2002-03-20 Benzoaxathiepin derivatives and their use as medicines
JP2002579452A JP4508531B2 (en) 2001-03-22 2002-03-20 Benzoxathiepine derivatives and their pharmaceutical use
EP02759802A EP1370547B1 (en) 2001-03-22 2002-03-20 Benzoaxathiepin derivatives and their use as medicines
AU2002308105A AU2002308105B2 (en) 2001-03-22 2002-03-20 Benzoaxathiepin derivatives and their use as medicines
DE60201264T DE60201264T2 (en) 2001-03-22 2002-03-20 BENZOAXATHIEPINE DERIVATIVES AND THEIR MEDICAL USE
US10/472,728 US7109234B2 (en) 2001-03-22 2002-03-20 Benzoxathiepine derivatives and their use as medicines
AT02759802T ATE276240T1 (en) 2001-03-22 2002-03-20 BENZOAXATHIEPINE DERIVATIVES AND THEIR MEDICAL USE
MXPA03008570A MXPA03008570A (en) 2001-03-22 2002-03-20 Benzoaxathiepin derivatives and their use as medicines.
PCT/FR2002/000969 WO2002081464A1 (en) 2001-03-22 2002-03-20 Benzoaxathiepin derivatives and their use as medicines
ZA200307362A ZA200307362B (en) 2001-03-22 2003-09-22 Benzoxathiepine derivatives and their use as medicaments.

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0103877A FR2822467B1 (en) 2001-03-22 2001-03-22 BENZOXATHIEPIN DERIVATIVES AND THEIR USE AS MEDICAMENTS

Publications (2)

Publication Number Publication Date
FR2822467A1 FR2822467A1 (en) 2002-09-27
FR2822467B1 true FR2822467B1 (en) 2003-12-12

Family

ID=8861426

Family Applications (1)

Application Number Title Priority Date Filing Date
FR0103877A Expired - Fee Related FR2822467B1 (en) 2001-03-22 2001-03-22 BENZOXATHIEPIN DERIVATIVES AND THEIR USE AS MEDICAMENTS

Country Status (16)

Country Link
US (1) US7109234B2 (en)
EP (1) EP1370547B1 (en)
JP (1) JP4508531B2 (en)
CN (1) CN1264836C (en)
AT (1) ATE276240T1 (en)
AU (1) AU2002308105B2 (en)
BR (1) BRPI0208324B1 (en)
CA (1) CA2441534C (en)
DE (1) DE60201264T2 (en)
DK (1) DK1370547T3 (en)
ES (1) ES2227481T3 (en)
FR (1) FR2822467B1 (en)
MX (1) MXPA03008570A (en)
PT (1) PT1370547E (en)
WO (1) WO2002081464A1 (en)
ZA (1) ZA200307362B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2868779B1 (en) * 2004-04-09 2008-08-22 Pierre Fabre Medicament Sa PROCESS FOR SYNTHESIS AND INTERMEDIATES OF BENZOXATHIEPINES
EP2243768A1 (en) * 2009-04-22 2010-10-27 Zylum Beteiligungsgesellschaft mbH & Co. Patente II KG Phenolic diazonium salt, method for its production and its application
FR2979823B1 (en) * 2011-09-13 2013-09-27 Pf Medicament USE OF 3- (R) - [3- (2-METHOXYPHENYLTHIO) -2- (S) -METHYL-PROPYL] AMINO-3,4-DIHYDRO-2H-1,5-BENZOXATHIEPINE FOR THE TREATMENT OF CANCER AND IN PARTICULAR FOR THE PREVENTION AND / OR TREATMENT OF CANCER METASTASES
FR2979822B1 (en) 2011-09-13 2015-05-08 Pf Medicament USE OF 3- (R) - [3- (2-METHOXYPHENYLTHIO) -2- (S) -METHYL-PROPYL] AMINO-3,4-DIHYDRO-2H-1,5-BENZOXATHIEPINE FOR PREVENTION AND / OR TREATMENT CARDIOTOXIC EFFECTS DUE TO CHEMOTHERAPY AND / OR RADIATION
FR3001151B1 (en) * 2013-01-21 2016-04-08 Pf Medicament ASSOCIATION OF A SLOW SODIUM CURRENT BLOCKER AND A SINUSAL IF CURRENT INHIBITOR AND THE PHARMARCEUTICAL COMPOSITIONS CONTAINING SAME

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK166779B1 (en) * 1983-12-14 1993-07-12 Takeda Chemical Industries Ltd 1,5-BENZOXATION PINE DERIVATIVES OR PHARMACEUTICAL ACCEPTABLE SALTS THEREOF, AND PHARMACEUTICAL PREPARATIONS CONTAINING SUCH A CONNECTION
US5538974A (en) * 1994-01-27 1996-07-23 Senju Pharamceutical Co., Ltd. Ophthalmic composition for lowering intraocular pressure

Also Published As

Publication number Publication date
EP1370547B1 (en) 2004-09-15
BR0208324A (en) 2004-03-09
DK1370547T3 (en) 2005-01-17
ZA200307362B (en) 2004-07-07
JP2004538261A (en) 2004-12-24
AU2002308105B2 (en) 2008-06-05
WO2002081464A1 (en) 2002-10-17
BRPI0208324B1 (en) 2016-12-20
FR2822467A1 (en) 2002-09-27
US7109234B2 (en) 2006-09-19
CN1505623A (en) 2004-06-16
ES2227481T3 (en) 2005-04-01
US20040127552A1 (en) 2004-07-01
DE60201264T2 (en) 2005-09-29
MXPA03008570A (en) 2004-05-21
JP4508531B2 (en) 2010-07-21
CN1264836C (en) 2006-07-19
EP1370547A1 (en) 2003-12-17
PT1370547E (en) 2005-02-28
CA2441534A1 (en) 2002-10-17
DE60201264D1 (en) 2004-10-21
ATE276240T1 (en) 2004-10-15
CA2441534C (en) 2011-08-09

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Legal Events

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ST Notification of lapse

Effective date: 20061130